Azo dyestuffs and method of preparing same



Patented l8,

RAJINAIJ) smenrmli orfmcmisran, E GLAND, ASSIGNOR}: 'ro IllflEBIALcnnmroanmnusrnrnsk LrrnrED, or WESTMINSTER, EN LAND IiYEsrUFi's alu ij'im'rnon OF rrmrnnrma SAME no'm'awing. Application 'aieah g sticed-serial n 475,764, and in Great mailman as, 1929.

- The present invention relates to the manufacture and application oinew azo' dyes,

' particularly adapted for the' dyeing of regeneratedcellulose silk, forexample; viscose silk, in even shades. 1 .5.

' According to the invention new 'di'sazo dyes which have the valuablepropertyofdyeing regenerated cellulose silk in even; shades are obtainedby coupling the product ofzdiazo 10 tization of a p-aminoazocompoundwith 1-amino-5naphthol-7-sulphonic acid or an N-substitutedderivative thereof. In the term p-aminoazo compoundI include anycompound containing the azo grou N N, and the amino roup. NH situate inthe por la-position t ereto, such as may be obtained, for examp1e, bycou ling agdiazoe tized aromatic am1ne,flor a? omologue orderivativethereof, with asuita ble coupling component containing anamino a group; vThe amino-azo compound may-contain, it wi11'be;understoodfsiibstituent groups,"wh'ich may be introduced beforeor'after. the components are coupledif The new dyes maybeillustratedbythe general formula; I

ga examples,'to which however a is m 11m;-

The parts are by weightfi I m 'pz jl jparts of--'1-amin05-naphthol-75sulphonic-acid aredissolved in water with about; 500 partsof'sodium carbonate. {The solu tion is cooled with ice and there isrun'in while stirring the diazo-suspension"obtained o in the known manner bydiazotizin'g the aminoazof idyestufis prepared by coupling 93 partsofjdiazotized'aniline with 223 parts of a" technical mixture ofa-naphthylamine-fiand T-sulphonic acids inthe usual way. The a mixtureis maintained alkaline and stirred 9 until coupling is complete when itis heated up and the dyestuifs isolated by the addition of common salt,It dyes viscose silk a greenish blue shade. i

It probably has" the following formula: l

, I V 0H i it 1:1 Ewamplefl r g T153" parts of aminosalicylic acidobtained on reduction of a technicalmixture of nitrosalicylic-acids arediazotized and combined; in the usual way with 143 partsof, oL-naplithylamine. 'The resulting aminoazfo;comf poundis diazotized with69partsof sodium V nitrite'and 250 parts of; 36% hydrochloric acid intheknown manner and the suspension of diazo-azo compound is slowly added toa cold well stirred solution of l-benzoyl-amino-51n-aphthol;7,-sulphonic acid, which is ;ke'pt faintly alkalinewithsodium carbonate throughout the coupling. When combination is completethe mixture isheated up and thedyestufi isolated by theaddition ofcomm-on salt. It dyes viscose silk a navy blue shade.

It probably has the following formula:

HO NaOsS I OONB NH.ooo.H|

and "OH I on Naoo'o N=N- N= N NaOgS 2 I I I I f];

I NH.OOCOH&

Exam-M63 The, amino-azo, dyestuff obtained by diazotizing 218 parts ofpara-nitroaniline o-sul phonic acid and coupling with 137 parts ofm-amino-p-cresol methyl ether is diazotiz'ed according to the knownmanner with about 69 parts of sodium nitrite and 300 parts of 36%hydrochloric acid and thesuspensi-on so obtained is stirred into a coldsolution of 239 parts, of 1 -amino- 5-naphthol-7-sulphon-ic acidcontaining about 400 parts of sodium carbonate. The mixture which ismaint'ained alkaline throughout is stirred until coupling is completeand is then heated up andthe dyestuif isolated by the addition of commonsalt. It dyes .viscos-e silk a greenish blue ha f I I fIt probably hasthe following formula;

The invention is further illustrated by the examples in the followingtable:

it will fibe' understood that, while the formulas given herein in allprobability correctly represent the dyes of the present insemen, theinvention is wholly independent "or the eor'r'eemees of such formulas.

I many apparently widely different em- 'bodiments er this "invention maybe made .without departing from the spirit thereof,

it is to be understoodthat I do not limit myself to the foregoingexamples or descriptions except as indicated in the followingpatentclaims. 1 :1 rclaim': I I 1. The process of prepari ng a disazodyestuff which comprises coupling the product of "diazotization ofap-aminoazo compound ofthe benzene and naphthalene series with anamfino-naphthol-sulfdnic acid of the genei'al formula I 1 Hols in which It"represents hydrogen or'a' ,raai cal of thebeiizene 's eries.'L I

The process-"of preparing a 'disazo dyestair whiehfcompr'is'es couplingthe product diefziotization'of "a p-aminoazo compound of the benzene"and naphthalene series with a 1 amino fi naplithol T-sulphonic acid; II

3. The process of claim 1 I wherein the perm-imam compound is "'areaction product of a diazotized amino compound "of the benzene seriesand an a-naphthylamine.

4:. The process. of claim 1 wherein the p-aminoazo compound is'a"reaction product of diazotized pi-nitroaniline-o-sulphonic acid andm-amin'oep crsol methyl ether.

'5. The process of vclaim 1 wherein the p-aminoazo compound isp-aminoazo-benzen'e-"p sulphonie acid. I

'6. Adyes'tufl' having the. general formula Fine? 7 I I "mm 7 in which'Rand "R "represent aromatic or.- ganicradicals of the benzene ornaphthalene series, and R" represents hydrogen or a. radical of thebenzene series;

7. A disazo dyestufi prepared by coupling the product of diazotizationof a p-aminoazo compound of the benzene and naphthalene series with anamino-naphthol-s ulphonic acid of the general formula NHR" in which Rrepresents hydrogen or a radical of the benzene series.

In testimony whereof, I aflix my signa-

